The objects of bioscience and biotechnology are apparently organic compounds. Thus, this lecture systematically and comprehensively describes fundamental topics necessary for the use of or the research on organic compounds, including the knowledge and theory on their nomenclature, nature, analysis, reactions, synthesis, and utility. The contents consist of the IUPAC nomenclature, the electronic states and bonding of molecules, three-dimensional structures of molecules, the instrumental analysis of molecular structures (NMR, IR, Ms), reactions of each functional group, the carbon-carbon bond formation and organic synthesis, and utility of natural and artificial organic compounds, which will be lectured according to the textbook, with the theoretical background and relationship between the topics being mentioned.
At the outset, this course allows the student to firmly learn the general knowledge and theory common to individual topics, such as the nomenclature of compounds, electronic states and bonding of molecules and their nature and structures owing to the former, and the electronic theory of organic chemistry essential to the description of reaction mechanisms. At the next stage, the students will proceed to study reactions unique to each functional group and the instrumental analysis of molecular structures, which are not only memorized but also well interpreted by them on the basis of the above general notion. While reviewing the previous two steps, the students are requested to increase their ability to understand the application of the fundamental topics, for example, the synthesis of organic compounds and utility of natural and artificial compounds. As a whole, this lecture will provide students basic knowledge and theory of organic chemistry and, at the same time, its covering area of utility of organic compounds.
Organic Chemistry II (alcohols, alkenes) aims to guide students in the world of biomolecules by getting them to learn the synthetic methods, properties, and reaction mechanisms of alcohols and ethers, which contain C, H, and O atoms, three out of four essential atoms in proteins, nucleic acids, and oligosaccharides. The course will also cover alkenes, C=C, a ubiquitous functional group in biomolecules. Understanding of alkenes is significant, because they are exploited as intermediates to useful materials. Two important instrument-based measurements, nuclear magnetic resonance spectra (NMR) and infrared spectra (IR), are also covered.
By the end of this course, students will be able to:
1. Understand that the O-H bond of alcohols tends to dissociate into an O anion and proton.
2. Recognize that the oxidation of alcohols gives aldehydes.
3. Learn how alcohols are synthesizable by the addition reactions of organometallic reagents, such as Grignard reagents, with carbonyl compounds, and by the addition reactions with alkenes.
4. Learn how alcohols are derivatizable into haloalkanes, esters, and ethers.
5. Learn how alcohols, ethers, and carbonyl coupounds can be synthesized by the addition reactions with alkenes.
6. Learn how these synthetic compounds are identified by using NMR, IR, and mass spectra.
alcohol, ether, alkene, NMR, IR, mass spectra
|✔ Specialist skills||Intercultural skills||Communication skills||Critical thinking skills||Practical and/or problem-solving skills|
The lecture is to be done in order according to the textbook. (Thus, students are encouraged to familiarize the expected pages of the textbook in advance to the class and to review them after the class.) Students are given concise exercise problems for the last 10 minutes of each class, and their solutions and remarks will be explained at the beginning of the next class.
|Course schedule||Required learning|
|Class 1||Properties of alcohols||Nomencrature, structure, and physical properties of alcohols|
|Class 2||Synthesis of alcohols||Nucleophilic substitution reaction, reduction of aldehyde|
|Class 3||Grignard reaction||Organnometallics, synthetic strategy|
|Class 4||Reaction of alcohols||Reaction with acid and base, rearrangement reaction, esters, haloalkanes|
|Class 5||Synthesis of ethers||Nomencrature, structure, and physical properties of ehters, Williamson ether synthesis|
|Class 6||Reaction of ethers||Oxacyclopropane (epoxide)|
|Class 7||Proton NMR||Mechanisms of nuclear magnetic resonance|
|Class 8||Chemical shift and spin splitting||Analysis of molecular structure|
|Class 9||Carbon-13 NMR and its application||Correlation spectroscopy|
|Class 10||Structure of alkenes||Nomencrature, structure, and physical properties of alkenes|
|Class 11||IR spectroscopy||Bond vibrations|
|Class 12||Mas spectroscopy||Measurement of molecular weight, fragmentation, Degree of unsaturation|
|Class 13||Reaction of alkenes 1||pi bonds, hydrogenation, halogenation, oxymercuration|
|Class 14||Reaction of alkenes 2||Hydroboration, diazomentane, carbenes, epoxidation|
|Class 15||Reaction of alkenes 3||Osmium tetroxide, ozonolysis, radical reactions|
Organic Chemistry - Structure and Function, 6th ed., K. P. C. Vollhardt and N, E. Schore, W. H. Freeman and Co., New York, 2011; The Japanese translation, 6th ed., Kagakudojin, Kyoto, 2011. (Japanese)
Study Guide and Solutions - Manual for Organic Chemistry, 6th ed., N, E. Schore, W. H.
Students will be assessed on the concise exercise problems in each class (30%) and the final exam (70%).
As there is no duplication of the contents from Organic Chemistry I (alkanes and haloalkanes) to IV (carbonyl compounds and amines), the systematic study in this order will maximize its efficiency. Therefore, students are advised to enroll all of them in serial order. After completion of these courses, more advanced lectures, Bioorganic Chemistry and Pharmaceutical Chemistry, are available. Thus, students can proceed to the higher level of organic chemistry by taking one or both of them, dependent on their interest.